JP2018188604A - Ester oil composition and its production method - Google Patents
Ester oil composition and its production method Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 67
- 239000010696 ester oil Substances 0.000 title claims abstract description 63
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims abstract description 76
- 229910003472 fullerene Inorganic materials 0.000 claims abstract description 76
- 239000002199 base oil Substances 0.000 claims abstract description 59
- 239000000654 additive Substances 0.000 claims abstract description 56
- 230000000996 additive effect Effects 0.000 claims abstract description 49
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 239000002245 particle Substances 0.000 claims abstract description 16
- -1 pentaerythritol fatty acid ester Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 238000002485 combustion reaction Methods 0.000 claims description 3
- 239000010687 lubricating oil Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 230000000630 rising effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 238000005259 measurement Methods 0.000 description 10
- 239000002994 raw material Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- 239000005069 Extreme pressure additive Substances 0.000 description 4
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000010705 motor oil Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 1
- XQHFZYPMZPUCII-UHFFFAOYSA-N C(CCC(=O)O)(=O)O.C(C1=CC=CC=C1)N Chemical class C(CCC(=O)O)(=O)O.C(C1=CC=CC=C1)N XQHFZYPMZPUCII-UHFFFAOYSA-N 0.000 description 1
- 101000823778 Homo sapiens Y-box-binding protein 2 Proteins 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- WJXJCXUHGUDZLX-UHFFFAOYSA-N P(=O)(OCCCC)(OCCCC)OCCCC.C(C)(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C Chemical compound P(=O)(OCCCC)(OCCCC)OCCCC.C(C)(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C WJXJCXUHGUDZLX-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
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- 238000012790 confirmation Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000005608 naphthenic acid group Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- Lubricants (AREA)
Abstract
Description
本発明は、フラーレン含有エステル油組成物及びその製造方法に関する。 The present invention relates to a fullerene-containing ester oil composition and a method for producing the same.
エステル油は，潤滑性，耐熱性，低温流動性，難燃性，生分解性に優れているため，環境問題に対応する潤滑油基油等として飛躍的に増加している。エステル油にはその用途に適するように特性を改善するために、酸化防止剤、極圧添加剤、錆び止め添加剤、腐食防止剤など添加剤が添加されている。 Ester oils have increased dramatically as lubricating base oils that respond to environmental problems because they are excellent in lubricity, heat resistance, low-temperature fluidity, flame retardancy, and biodegradability. Additives such as antioxidants, extreme pressure additives, rust inhibitors, and corrosion inhibitors are added to ester oils in order to improve their properties to suit the application.
更に、潤滑効果を向上するためにフラーレンをエステル油に添加することも試みられている。しかし、フラーレンが、潤滑基油として使用される鉱油、エステル油等には溶解しにくいため、フラーレンを溶かすトルエンなど有機溶媒にあらかじめ溶解するなどの工夫が試みられてきた。 In addition, it has been attempted to add fullerene to ester oil in order to improve the lubricating effect. However, since fullerenes are difficult to dissolve in mineral oils, ester oils and the like used as lubricating base oils, attempts have been made to dissolve them in advance in an organic solvent such as toluene that dissolves fullerenes.
特許文献１には、カルボン酸とヒンダード有機ポリオールとの反応生成物である合成エステル、１種以上の追加の基油および添加剤パッケージを含有する潤滑剤が開示されている。 Patent Document 1 discloses a lubricant containing a synthetic ester that is a reaction product of a carboxylic acid and a hindered organic polyol, one or more additional base oils, and an additive package.
特許文献２には、「高温用途での使用に適した多価アルコールエステル潤滑剤のための、少なくとも高分子アミン系酸化防止剤およびホウ酸含有極圧／耐摩耗剤を含む、改良された添加剤パッケージを提供する。潤滑流体は、多価アルコールと、大部分の割合を占める３，５，５−トリメチルヘキサン酸（ｉｓｏ−Ｃ９酸）を含むモノカルボン酸混合物との反応生成物であるベースストックを含む。潤滑剤の最大約２０重量パーセントまで添加剤パッケージを添加し、４０℃で少なくとも約１４０ ｃＳｔおよび１００℃で約１５．０ｃＳｔ以上の潤滑剤の粘度を提供し得る。グリースは、高粘度の潤滑流体に増粘剤を添加することにより形成される。」ことが開示されている。 In US Pat. No. 6,057,049, “Improved additions for polyhydric alcohol ester lubricants suitable for use in high temperature applications, including at least polymeric amine antioxidants and boric acid containing extreme pressure / antiwear agents. The lubricant fluid is a base that is the reaction product of a polyhydric alcohol and a monocarboxylic acid mixture comprising a major portion of 3,5,5-trimethylhexanoic acid (iso-C9 acid). The additive package can be added up to about 20 weight percent of the lubricant to provide a lubricant viscosity of at least about 140 cSt at 40 ° C. and about 15.0 cSt or higher at 100 ° C. "It is formed by adding a thickener to a lubricating fluid of viscosity".
また、特許文献３には、「フラーレンを高濃度かつ安定に溶解した飽和炭化水素溶液を調製することができるフラーレンの飽和炭化水素溶液の製造方法。フラーレンをトルエンまたはシクロヘキサンに予め溶解させ、この溶液と飽和炭化水素とを混合し、この混合液からトルエンまたはシクロヘキサンを減圧留去してフラーレンを溶解する飽和炭化水素溶液の調製。」ことが開示されている。 Patent Document 3 discloses that “a method for producing a saturated hydrocarbon solution of fullerene capable of preparing a saturated hydrocarbon solution in which fullerene is dissolved in high concentration and stably. This solution is prepared by dissolving fullerene in toluene or cyclohexane in advance. And a saturated hydrocarbon are mixed, and toluene or cyclohexane is distilled off from this mixture under reduced pressure to prepare a saturated hydrocarbon solution in which fullerene is dissolved.
しかし、一般的に用いられてきた添加剤を含有させると、エステル油組成物の粘度が上昇してしまう。粘度上昇のため、エステル油組成物の低温流動性が悪くなり、均一な油膜を形成することが困難となる。また、粘度上昇と共に、粘性抵抗が増加し、省エネルギー効果の観点からは好ましくない。さらに、高速で使用する場合には、粘度上昇による発熱の増加も問題になる。 However, the inclusion of commonly used additives increases the viscosity of the ester oil composition. Due to the increase in viscosity, the low temperature fluidity of the ester oil composition deteriorates, making it difficult to form a uniform oil film. In addition, the viscosity resistance increases with increasing viscosity, which is not preferable from the viewpoint of energy saving effect. Further, when used at high speed, an increase in heat generation due to an increase in viscosity becomes a problem.
本発明者らは、以上の事情に鑑みてなされたものであり、添加剤を配合していても粘度の上昇が抑えられるエステル油組成物を提供することを課題としている。 The present inventors have been made in view of the above circumstances, and an object of the present invention is to provide an ester oil composition capable of suppressing an increase in viscosity even when an additive is blended.
本発明は以下［１］〜［６］の発明を含む。
［１］ エステル油（以下、「基油」という。）、芳香族環を有する添加剤、及びフラーレンを含み、１０ｍｌあたりの長径１μｍ以上の粒子が平均１個未満であることを特徴とするエステル油組成物。
［２］ フラーレンの濃度が基油に対して０．００１〜１．０質量％、芳香族環を有する添加剤の濃度が基油に対して０．００１〜６．０質量％であることを特徴とする前項［１］に記載のエステル油組成物。
［３］ 前記基油がペンタエリスリトール脂肪酸エステルを含むことを特徴とする前項［１］または［２］に記載のエステル油組成物。
［４］ 前記基油が炭素数６〜１２の一価飽和脂肪族アルコールと炭素数が６〜１２の一価飽和脂肪族カルボン酸からなるモノエステルを含むことを特徴とする前項［１］または［２］に記載のエステル油組成物。
［５］ 前記エステル油組成物は、内燃機関用、工業用潤滑油である前項［１］〜［４］に記載のエステル油組成物。
［６］ 基油と原料フラーレンとを混合しフラーレンを基油中に抽出する工程と、不溶成分を除去する工程と、添加剤と基油とを混合する工程を含むことを特徴とする前項［１］〜［５］に記載のエステル油組成物の製造方法。
The present invention includes the following [1] to [6].
[1] An ester comprising an ester oil (hereinafter referred to as “base oil”), an additive having an aromatic ring, and fullerene, and having an average of less than 1 particle having a major axis of 1 μm or more per 10 ml Oil composition.
[2] The concentration of fullerene is 0.001 to 1.0 mass% with respect to the base oil, and the concentration of the additive having an aromatic ring is 0.001 to 6.0 mass% with respect to the base oil. The ester oil composition according to item [1], which is characterized by the following.
[3] The ester oil composition as described in [1] or [2] above, wherein the base oil contains a pentaerythritol fatty acid ester.
[4] The above item [1], wherein the base oil contains a monoester composed of a monovalent saturated aliphatic alcohol having 6 to 12 carbon atoms and a monovalent saturated aliphatic carboxylic acid having 6 to 12 carbon atoms. The ester oil composition according to [2].
[5] The ester oil composition according to [1] to [4], wherein the ester oil composition is an internal combustion engine or industrial lubricating oil.
[6] The preceding item characterized by including a step of mixing base oil and raw material fullerene and extracting fullerene into the base oil, a step of removing insoluble components, and a step of mixing the additive and the base oil. The manufacturing method of the ester oil composition as described in 1]-[5].
本発明によれば、添加剤を添加していても粘度の向上が抑えられるエステル油組成物を提供することができる。 According to the present invention, it is possible to provide an ester oil composition in which an increase in viscosity is suppressed even when an additive is added.
以下、本発明の実施形態に係るエステル油組成物について説明する。
本発明の実施形態に係るエステル油組成物は、エステル油（以下、「基油」という。）、芳香族環を有する添加剤、及びフラーレンを含み、１０ｍｌあたりの長径１μｍ以上の粒子が平均１個未満である。
Hereinafter, the ester oil composition according to the embodiment of the present invention will be described.
The ester oil composition according to an embodiment of the present invention includes an ester oil (hereinafter referred to as “base oil”), an additive having an aromatic ring, and fullerene, and particles having a major axis of 1 μm or more per 10 ml average 1 Less than
（基油）
基油としては種々のエステル油を用いることができる。例えば、エステル結合を有するもので、モノエステル、ジエステル、ポリオールエステル、コンプレックエステルなどが挙げられる。これらのエステル油は単独で使用しても良く、またこれらの中から選ばれる２種以上のエステル油を任意の割合で混合して使用してもよい。ペンタエリスリトール脂肪酸エステル、および炭素数が６〜１２の一価飽和脂肪族アルコールと炭素数が６〜１２の一価飽和脂肪族カルボン酸からなるモノエステルの少なくとも一種を含むことが好ましい。さらに、下記式（１）で表されるペンタエリスリトール脂肪酸エステル、及び下記式（２）で表記されるモノエステルの少なくとも一種を含むことがより好ましい。
Ｃ（ＣＨ２ＯＣＯＲ）４ （１）
Ｒ２ＣＨ（Ｃ２Ｈ５）ＣＯＯＣＨ２（Ｃ２Ｈ５）Ｒ１ （２）
式（１）中、Ｒは炭素数４〜１２のアルキル基、好ましくは炭素数４〜８のアルキル基である。式（２）中、Ｒ１及びＲ２は炭素数２〜８のアルキル基、好ましくは炭素数３〜５のアルキル基である。
(Base oil)
Various ester oils can be used as the base oil. For example, it has an ester bond, and monoester, diester, polyol ester, complex ester and the like can be mentioned. These ester oils may be used alone, or two or more kinds of ester oils selected from these may be mixed and used in an arbitrary ratio. It is preferable to include at least one of pentaerythritol fatty acid ester and monoester composed of monovalent saturated aliphatic alcohol having 6 to 12 carbon atoms and monovalent saturated aliphatic carboxylic acid having 6 to 12 carbon atoms. Furthermore, it is more preferable to include at least one of pentaerythritol fatty acid ester represented by the following formula (1) and monoester represented by the following formula (2).
C (CH 2 OCOR) 4 (1)
R 2 CH (C 2 H 5 ) COOCH 2 (C 2 H 5 ) R 1 (2)
In the formula (1), R is an alkyl group having 4 to 12 carbon atoms, preferably an alkyl group having 4 to 8 carbon atoms. In formula (2), R 1 and R 2 are alkyl groups having 2 to 8 carbon atoms, preferably alkyl groups having 3 to 5 carbon atoms.
（芳香族環を有する添加剤）
芳香族環を有する、粘度指数向上剤、清浄分散剤、流動点降下剤、極圧添加剤、固体潤滑剤、油性向上剤、酸化防止剤、さび止め添加剤、抗乳化剤、腐食防止剤などが添加剤として使用できる。具体的に、粘度指数向上剤としては、ポリアルキルスチレン、スチレン−ジエンコポリマーの水素化物添加剤など、清浄分散剤としては、ベンジルアミンコハク酸誘導体、アルキルフェノールアミン類など、流動点降下剤としては、塩素化パラフィン−ナフタレン縮合物、塩素化パラフィンーフェノール縮合物、ポリアルキルスチレン系など、極圧添加剤としては、トリフェニルフォスフェート、ジベンジルジサルファイド、アリールリン酸エステル、アリール亜リン酸エステル、アリールリン酸エステルのアミン塩、アリールチオリン酸エステル、アリールチオリン酸エステルのアミン塩、ナフテン酸など、酸化防止剤には、ヒンダードフェノール、芳香族アミン、例えば、ジブチルヒドロキシトルエン（ＢＨＴ）、ブチルヒドロキシアニソール（ＢＨＡ）、２，６−ジ−ｔ−ブチル−パラクレゾール（ＤＢＰＣ）、３−アリールベンゾフランー２−オン（ヒドロキシカルボン酸の分子内環状エステル）、フェニル−α−ナフチルアミン、ジアルキルジフェニルアミン、ベンゾトリアゾールなど、抗乳化剤には、アルキルベンゼンスルホン酸塩など、腐食防止剤としては、ベンゾトリアゾール及びその誘導体、ジアルキルナフタレンスルホン酸塩などを挙げることができる。
(Additives with aromatic rings)
Has aromatic ring, viscosity index improver, detergent dispersant, pour point depressant, extreme pressure additive, solid lubricant, oiliness improver, antioxidant, rust inhibitor, anti-emulsifier, corrosion inhibitor, etc. Can be used as an additive. Specifically, as a viscosity index improver, polyalkyl styrene, hydride additive of styrene-diene copolymer, etc., as a cleaning dispersant, benzylamine succinic acid derivatives, alkylphenol amines, etc., as pour point depressants, Chlorinated paraffin-naphthalene condensate, chlorinated paraffin-phenol condensate, polyalkylstyrene, etc. Extreme pressure additives include triphenyl phosphate, dibenzyl disulfide, aryl phosphate ester, aryl phosphite ester, aryl phosphorus Antioxidants, such as amine salts of acid esters, aryl thiophosphates, amine salts of aryl thiophosphates, and naphthenic acids, include hindered phenols, aromatic amines such as dibutylhydroxytoluene (BHT), butylhydroxyanisate. (BHA), 2,6-di-t-butyl-paracresol (DBPC), 3-arylbenzofuran-2-one (an intramolecular cyclic ester of hydroxycarboxylic acid), phenyl-α-naphthylamine, dialkyldiphenylamine, Examples of demulsifiers such as benzotriazole include alkylbenzene sulfonates, and examples of corrosion inhibitors include benzotriazole and derivatives thereof, and dialkylnaphthalene sulfonates.
また、芳香族環を有する添加剤は、エステル油組成物の使用形態に合わせて抗酸化剤、極圧添加剤として働くものであることが好ましい。上記の添加剤は単独で添加しても良く、これらの中から選ばれる２種以上の添加剤を配合することもよい。 Moreover, it is preferable that the additive which has an aromatic ring functions as an antioxidant and an extreme pressure additive according to the usage form of an ester oil composition. Said additive may be added independently and it is also good to mix | blend 2 or more types of additives chosen from these.
本実施形態におけるエステル油組成物中、芳香族環を有する添加剤の濃度は基油に対して好ましくは０．０１〜６質量％であり、より好ましくは０．０１〜４質量％であり、さらに好ましくは０．０１〜３質量％である。芳香族を有する添加剤の濃度が０．０１質量％以上であれば、添加剤としての効果、フラーレンの溶解を促進する効果及び、フラーレンの凝集を抑制する効果が発揮できる。芳香族環を有する添加剤の濃度が６質量％以下であれば、添加剤の添加による粘度の上昇が十分抑制できる。 In the ester oil composition in the present embodiment, the concentration of the additive having an aromatic ring is preferably 0.01 to 6% by mass, more preferably 0.01 to 4% by mass with respect to the base oil, More preferably, it is 0.01-3 mass%. When the concentration of the aromatic additive is 0.01% by mass or more, the effect as an additive, the effect of promoting the dissolution of fullerene, and the effect of suppressing the aggregation of fullerene can be exhibited. If the density | concentration of the additive which has an aromatic ring is 6 mass% or less, the raise of the viscosity by addition of an additive can fully be suppressed.
（フラーレン）
本実施形態では、種々のフラーレンを用いることができる。例えば、Ｃ６０やＣ７０、さらに高次のフラーレン、あるいはそれらの混合物が挙げられる。入手しやすいことから、フラーレンの中でもＣ６０及びＣ７０が好ましく、Ｃ６０がより好ましい。混合物の場合は、Ｃ６０が５０質量％以上含まれることが好ましい。
(Fullerene)
In the present embodiment, various fullerenes can be used. For example, C 60 or C 70 , higher order fullerene, or a mixture thereof can be used. Since easily available, preferably C 60 and C 70 Among fullerene, C 60 is more preferable. For mixtures, it is preferred that the C 60 is contained more than 50 wt%.
本実施形態におけるエステル油組成物中、フラーレンは凝集が少なく、エステル油組成物１０ｍｌあたり長径１μｍ以上の粒子が１個未満である。この確認は、後述する実施例の方法により行うことができる。 In the ester oil composition in the present embodiment, fullerene is less agglomerated, and less than one particle having a major axis of 1 μm or more per 10 ml of the ester oil composition. This confirmation can be performed by a method of an embodiment described later.
また、本実施形態におけるエステル油組成物中、フラーレンの濃度は、好ましくは０．００１〜１質量％であり、より好ましくは０．０５％〜０．６質量％であり、更に好ましくは０．０５％〜０．４質量％である。フラーレン濃度が０．００１質量％以上であれば、摩擦係数低減，及び添加剤の添加による粘度上昇を抑効する果が十分期待できる。フラーレンの濃度が１質量％以下であれば、長時間放置しても凝集粒が析出する可能性がさらに少なくなる。 In the ester oil composition of the present embodiment, the fullerene concentration is preferably 0.001 to 1% by mass, more preferably 0.05% to 0.6% by mass, and still more preferably 0.8. It is 05% to 0.4% by mass. If the fullerene concentration is 0.001% by mass or more, the effect of reducing the friction coefficient and suppressing the increase in viscosity due to the addition of the additive can be sufficiently expected. If the fullerene concentration is 1% by mass or less, the possibility that aggregated particles precipitate even if left for a long time is further reduced.
（製造方法）
本実施形態のエステル油組成物の製造方法は、基油とフラーレンとを混合し、フラーレンを基油中に抽出し、基油とフラーレンとの混合物を得る第一工程と、前記混合物に含まれる不溶物を除去し、フラーレン溶液を得る第二工程と、第二工程で得たフラーレン溶液を基油で希釈し、最終的に得られるエステル油組成物中のフラーレン濃度を調整する第三工程と、芳香族を有する添加剤（以下、特に断りのない限り「添加剤」という）をいずれかの工程の基油に添加する第四工程を含む。ここで、第四工程は、第一工程前〜第三工程後のいずれかの段階で実施されればよい。
(Production method)
The method for producing an ester oil composition of the present embodiment includes a first step of mixing a base oil and fullerene, extracting the fullerene into the base oil to obtain a mixture of the base oil and fullerene, and the mixture. A second step of removing insolubles and obtaining a fullerene solution; a third step of diluting the fullerene solution obtained in the second step with a base oil and adjusting the fullerene concentration in the ester oil composition finally obtained; And a fourth step of adding an additive having an aromatic (hereinafter referred to as “additive” unless otherwise specified) to the base oil of any step. Here, the fourth step may be performed at any stage after the first step to the third step.
（第一工程）
原料フラーレンと基油とを混合し、フラーレンを基油中に抽出する。好ましくは、室温付近または必要に応じて加温しながら、３〜４８時間、撹拌しながら前記抽出を行う。攪拌は、一般的な撹拌機でもよいが、好ましくは、超音波分散装置、ホモジナイザー、ボールミル、ビーズミルなどを用いて行うと短時間で所望のフラーレン濃度に抽出しやすい。原料フラーレンの仕込み量は、例えば、最終的に調製したいエステル油組成物のフラーレン濃度を考慮して、計算上基油に対して所望のフラーレン濃度が得られるフラーレン量の１．２〜５倍、より好ましくは１．２〜３倍とする。１．２倍以上とすることで、抽出可能な溶解物質の量が多くなり、所望のフラーレン濃度を短時間で得やすくなる。また、５倍以下とすることで、後述する第二工程で不要物の除去がし易くなる。さらに、原料フラーレンの消費が抑えられ経済的である。
(First step)
The raw material fullerene and the base oil are mixed, and the fullerene is extracted into the base oil. Preferably, the extraction is performed with stirring for about 3 to 48 hours while heating around room temperature or as necessary. Stirring may be performed using a general stirrer, but preferably, it is easy to extract to a desired fullerene concentration in a short time by using an ultrasonic dispersing device, a homogenizer, a ball mill, a bead mill, or the like. The amount of raw material fullerene charged is, for example, 1.2 to 5 times the amount of fullerene that gives a desired fullerene concentration relative to the base oil in consideration of the fullerene concentration of the ester oil composition to be finally prepared. More preferably 1.2 to 3 times. By setting it to 1.2 times or more, the amount of extractable dissolved substance increases, and a desired fullerene concentration can be easily obtained in a short time. Moreover, it becomes easy to remove an unnecessary thing by the 2nd process mentioned later by setting it as 5 times or less. Furthermore, the consumption of raw material fullerene is suppressed and it is economical.
（第二工程）
第一工程で得られた混合物には不溶物の粒子として、未溶解のフラーレンの凝集物、場合によっては基油の不純物、製造過程で混入した粒子などが含まれている。それら粒子は、フラーレンの凝集物を招き、また摺動部材等を摩耗させてしまうなどの不具合の原因となる恐れがある。そこで前記不溶物を除去する第二工程を設ける。第二工程としては、エステル油組成物１０ｍｌあたり長径１μｍ以上の粒子が１個未満になるまで前記不溶物を除去できればよく、例えば、濾過による除去方法、遠心分離による除去方法、それら除去方法の組み合わせなどを挙げることができる。処理時間の点から、少量のエステル油組成物を得る場合は濾過が好ましく、大量のエステル油組成物を得る場合は、遠心分離あるいは遠心分離後に濾過を用いることが好ましい。
(Second step)
The mixture obtained in the first step contains, as insoluble particles, undissolved aggregates of fullerene, possibly base oil impurities, particles mixed in the manufacturing process, and the like. These particles may cause an agglomeration of fullerene and cause problems such as wear of the sliding member. Therefore, a second step of removing the insoluble matter is provided. As the second step, it is sufficient that the insoluble matter can be removed until less than one particle having a major axis of 1 μm or more per 10 ml of the ester oil composition. For example, a removal method by filtration, a removal method by centrifugation, and a combination of these removal methods And so on. From the viewpoint of processing time, filtration is preferable when a small amount of ester oil composition is obtained, and when a large amount of ester oil composition is obtained, it is preferable to use filtration after centrifugation or centrifugation.
前記濾過による除去方法では、例えば、第一工程で得られたフラーレンと基油との混合物を孔径０．１〜１μｍのメンブランフィルターを用いて濾過することにより不溶物を除去し、フラーレン溶液として回収する。この濾過は吸引濾過または加圧濾過にすると時間短縮が図れるので好ましい。 In the removal method by filtration, for example, the mixture of fullerene and base oil obtained in the first step is filtered using a membrane filter having a pore size of 0.1 to 1 μm to remove insoluble matters and recovered as a fullerene solution. To do. This filtration is preferably performed by suction filtration or pressure filtration because the time can be shortened.
遠心分離による除去方法では、例えば、第一工程で得られたフラーレンと基油との混合物に対して遠心分離処理を施し上澄み部を不溶物除去後のフラーレン溶液として回収する。 In the removal method by centrifugation, for example, the mixture of fullerene and base oil obtained in the first step is subjected to centrifugation, and the supernatant is recovered as a fullerene solution after removal of insoluble matter.
（第三工程）
第二工程で得たフラーレン溶液を、該エステル油組成物中のフラーレン濃度が所望の濃度となるように、第一工程で用いた基油と同種類の基油または異種類の基油で希釈する。以下、特に断りのない限り、希釈を目的とする基油を「希釈基油」と言う。なお、第二工程で得たフラーレン溶液が所望の組成のエステル油組成物となっている場合は、第三工程を省略できる。
(Third process)
The fullerene solution obtained in the second step is diluted with the same type of base oil or a different type of base oil used in the first step so that the fullerene concentration in the ester oil composition becomes a desired concentration. To do. Hereinafter, unless otherwise specified, a base oil intended for dilution is referred to as a “diluted base oil”. In addition, when the fullerene solution obtained at the second step is an ester oil composition having a desired composition, the third step can be omitted.
（第四工程）
所望の添加剤濃度を有するエステル油組成物を得るために、第一工程前〜第三工程後のいずれかの段階で、基油（フラーレン等を含んでいてもよい。また、希釈基油でもよい。）と適量な添加剤とを混合し、好ましくは、室温又は必要に応じて加温条件下３０分〜２時間撹拌する。第四工程は、第一工程前〜第三工程後のいずれかの段階で1回又は複数回行ってもよい。
(Fourth process)
In order to obtain an ester oil composition having a desired additive concentration, a base oil (fullerene or the like may be contained at any stage before the first process to the third process). And a suitable amount of additives, and preferably stirred at room temperature or, if necessary, for 30 minutes to 2 hours under warming conditions. The fourth step may be performed once or a plurality of times at any stage before the first step to after the third step.
添加剤の添加量は、最終に得られるエステル油組成物において、所望する添加剤濃度になるように、適量に調整する。 The addition amount of the additive is adjusted to an appropriate amount so as to obtain a desired additive concentration in the finally obtained ester oil composition.
第四工程は、できるだけ早い工程で実施することが好ましい。例えば、第一工程前に、基油と添加剤とを混合し、添加剤を含有する基油を第一工程で用いると、フラーレンを第二工程で抽出しやすくし、時間短縮が図れる観点からより好ましい。 The fourth step is preferably performed as early as possible. For example, if base oil and additives are mixed before the first step and the base oil containing the additives is used in the first step, fullerenes can be easily extracted in the second step, and the time can be reduced. More preferred.
また、第三工程で、添加剤を含有する希釈基油を用いてもよい。希釈基油中の添加剤濃度を、第二工程で得たフラーレン溶液中の添加剤濃度と同じにしておくと、希釈基油による希釈率に、得られるエステル油組成物中の添加剤濃度が依存しなくなるので好ましい。 In the third step, a diluted base oil containing an additive may be used. If the additive concentration in the diluted base oil is the same as the additive concentration in the fullerene solution obtained in the second step, the additive concentration in the resulting ester oil composition is determined by the dilution rate with the diluted base oil. It is preferable because it does not depend.
（用途）
本実施形態のエステル油組成物は、内燃機関用、工業用潤滑油として使用ができる。具体的に、車用エンジン油、ディーゼルエンジン油、ガスエンジン油、発電エンジン油等；マシン油、軸受油、駆動伝達装置用油、冷凍機油、タービン油、油圧作動油、コンプレッサー油、ギヤ油、摺動面油などが挙げられる。
(Use)
The ester oil composition of this embodiment can be used as an internal combustion engine or industrial lubricating oil. Specifically, vehicle engine oil, diesel engine oil, gas engine oil, power generation engine oil, etc .; machine oil, bearing oil, drive transmission oil, refrigerator oil, turbine oil, hydraulic fluid, compressor oil, gear oil, Examples include sliding surface oil.
以上、本発明の好ましい実施の形態について述べたが、本発明は特定の実施の形態に限定されるものではなく、特許請求の範囲内に記載された本発明の要旨の範囲内において、種々の変形・変更が可能である。 The preferred embodiments of the present invention have been described above. However, the present invention is not limited to the specific embodiments, and various modifications can be made within the scope of the present invention described in the claims. Deformation / change is possible.
以下、本発明の実施例について説明する。なお、本発明は以下の実施例のみに限定されるものではない。 Examples of the present invention will be described below. In addition, this invention is not limited only to a following example.
（フラーレン濃度の測定）
フラーレンのエステル油溶液等を試料とし、試料中のフラーレンの濃度は、分光光度計（（株）島津製作所；紫外可視分光光度計ＵＶ−１７００）を用いて、試料をトルエンで希釈し、このトルエン溶液の３８１ｎｍにおける吸光度を測定することで実施した。なお、同種のフラーレンのトルエン溶液であらかじめ作成した検量線を用いた。
(Measurement of fullerene concentration)
A fullerene ester oil solution or the like is used as a sample, and the concentration of fullerene in the sample is diluted with toluene using a spectrophotometer (Shimadzu Corporation; UV-visible spectrophotometer UV-1700). The measurement was performed by measuring the absorbance of the solution at 381 nm. A calibration curve prepared in advance with a toluene solution of the same kind of fullerene was used.
（１μｍ以上の粒子数の測定）
エステル油組成物を３０℃で３日間放置後、その１０ｍｌを０．１μｍのメンブランフィルターで濾過し、メンブランフィルターの濾過面を走査型電子顕微鏡で観察し、長径１μｍ以上の粒子を数えた。この濾過〜走査型電子顕微鏡観察までを３回繰り返し、粒子数の平均値を得た。
(Measurement of the number of particles of 1 μm or more)
After leaving the ester oil composition at 30 ° C. for 3 days, 10 ml of the ester oil composition was filtered with a 0.1 μm membrane filter, and the filtration surface of the membrane filter was observed with a scanning electron microscope to count particles having a major axis of 1 μm or more. This filtration to scanning electron microscope observation was repeated three times to obtain an average value of the number of particles.
（粘度の測定）
回転粘度計（Ｂｒｏｏｋｆｉｅｌｄ製 デジタル粘度計 ＤＶ−Ｅ、スピンドルＳＣ４−１８、回転数５０ｒｐｍ）を用い、２５℃で、エステル油組成物を試料として粘度を測定した。なお、粘度上昇率は、試料に用いられている基油についても同様に粘度を測定し、以下の通り求めた。
粘度上昇率（％）＝（［試料の粘度］／［基油の粘度］−１）×１００
(Measurement of viscosity)
Using a rotational viscometer (Brookfield digital viscometer DV-E, spindle SC4-18, rotation speed 50 rpm), the viscosity was measured at 25 ° C. using the ester oil composition as a sample. In addition, the viscosity increase rate measured the viscosity similarly about the base oil used for the sample, and calculated | required as follows.
Viscosity increase rate (%) = ([viscosity of sample] / [viscosity of base oil] -1) × 100
（摩擦係数の測定）
エステル油組成物を試料として、ピンオンディスクトライボメーター（Ａｎｔｏｎｐａｒｒ製）を用いて、２５℃、荷重１０Ｎ、回転速度１０ｒｐｍ、回転数３００回の条件で摩擦係数を測定した。
(Measurement of friction coefficient)
Using the ester oil composition as a sample, a friction coefficient was measured using a pin-on-disk tribometer (manufactured by Antonparr) at 25 ° C., a load of 10 N, a rotation speed of 10 rpm, and a rotation speed of 300 times.
（材料）
以下の製品を各実施例・比較例で用いた。
（フラーレン）
原料フラーレン；フロンティアカーボン（株）製ｎａｎｏｍ（登録商標） ｍｉｘ ＳＴ（Ｃ６０：６０質量％、Ｃ７０：２５質量％、残部が他高次フラーレンの混合物。）
（基油）
エステル油Ａ；日油製ユニスター（登録商標）ＨＲ３２ （ポリオールエステル）
エステル油Ｂ；モービル社製ＥＡＬ Ａｒｃｔｉｃ３２ （ポリオールエステル）
（添加剤）
トリクレジルホスフェート；和光純薬工業（株）製 特級リン酸トリクレジル
ＢＨＴ；東京化成工業（株）製２，６−ジ−ｔｅｒｔ−ブチル−ｐ−クレゾール
リン酸トリブチル；東京化成工業（株）特級
ジアルキルジチオリン酸亜鉛；アデカ製：アデカキクルーブＺ−１１２
(material)
The following products were used in each example and comparative example.
(Fullerene)
Raw material fullerene: nanom (registered trademark) mix ST manufactured by Frontier Carbon Co., Ltd. (C 60 : 60% by mass, C 70 : 25% by mass, the balance being a mixture of other higher fullerenes.)
(Base oil)
Ester oil A; NOF UNISTAR (registered trademark) HR32 (polyol ester)
Ester oil B: EAL Arctic 32 (polyol ester) manufactured by Mobil
(Additive)
Tricresyl phosphate; manufactured by Wako Pure Chemical Industries, Ltd. Special grade tricresyl phosphate BHT; manufactured by Tokyo Chemical Industry Co., Ltd. 2,6-di-tert-butyl-p-cresol tributyl phosphate; special grade produced by Tokyo Chemical Industry Co., Ltd. Zinc dialkyldithiophosphate; manufactured by ADEKA: ADEKA CLUOVE Z-112
（実施例１）
基油Ａ２５０ｇと原料フラーレン０．３７５ｇとを混合し、室温でスターラーを用いて３６時間撹拌した。次に、孔径０．１μｍのメンブランフィルターで濾過して、フラーレンを含有した濾液約２５０ｇを得た。この濾液の、フラーレン濃度は０．１３５質量％であった。基油と同じ種類の希釈基油８８ｇを用いて、この濾液を希釈した。さらに、添加剤としてトリクレジルホスフェートを０．３３８ｇ添加し、スターラーを用いて、室温で１ｈ撹拌して溶解した。その結果、表１に記載のフラーレン濃度及び添加剤濃度を有するエステル油組成物を得た。なお、添加剤濃度は仕込量より計算をした。また、このエステル油組成物について表１に記載の測定を行った。
(Example 1)
250 g of base oil A and 0.375 g of raw material fullerene were mixed and stirred at room temperature using a stirrer for 36 hours. Next, it was filtered through a membrane filter having a pore size of 0.1 μm to obtain about 250 g of a filtrate containing fullerene. The fullerene concentration of this filtrate was 0.135% by mass. The filtrate was diluted with 88 g of diluted base oil of the same type as the base oil. Further, 0.338 g of tricresyl phosphate was added as an additive and dissolved by stirring for 1 h at room temperature using a stirrer. As a result, an ester oil composition having the fullerene concentrations and additive concentrations shown in Table 1 was obtained. The additive concentration was calculated from the charged amount. Moreover, the measurement of Table 1 was performed about this ester oil composition.
（実施例２〜６）
基油の種類、原料フラーレンの仕込み量、希釈基油の添加量、添加剤の種類、添加剤の添加量、及び添加剤の濃度を表１に示したように変えた以外は実施例１と同様の操作及び測定を行い、表１に記載した結果を得た。
(Examples 2 to 6)
Example 1 except that the type of base oil, the charged amount of raw material fullerene, the added amount of diluted base oil, the type of additive, the added amount of additive, and the concentration of the additive were changed as shown in Table 1. The same operation and measurement were performed, and the results described in Table 1 were obtained.
（比較例１〜２）
比較例１〜２は、基油Ａ及び基油Ｂを孔径０．１μｍのメンブランフィルターで濾過することのみ行い、得られた濾液をエステル油組成物として扱い、実施例１と同様に測定を行なった。
(Comparative Examples 1-2)
In Comparative Examples 1 and 2, only base oil A and base oil B were filtered through a membrane filter having a pore size of 0.1 μm, and the obtained filtrate was treated as an ester oil composition, and measurement was performed in the same manner as in Example 1. It was.
（比較例３）
比較例３は、基油Ａ２５０ｇを孔径０．１μｍのメンブランフィルターで濾過した。次に、添加剤トリクレジルホスフェート０．２５ｇを濾液に添加し、スターラーを用いて室温で１ｈ撹拌し、表１に記載の添加剤濃度を有するエステル油組成物を得た。実施例１と同様に測定を行なった。
(Comparative Example 3)
In Comparative Example 3, 250 g of base oil A was filtered through a membrane filter having a pore size of 0.1 μm. Next, 0.25 g of the additive tricresyl phosphate was added to the filtrate and stirred for 1 h at room temperature using a stirrer to obtain an ester oil composition having the additive concentrations shown in Table 1. Measurements were performed in the same manner as in Example 1.
（比較例４〜６）
基油の種類、添加剤の種類、添加剤の添加量、及び添加剤の濃度は表１に示したように変えた以外は比較例３と同様の操作及び測定を行い、結果を表１に記載した。
(Comparative Examples 4-6)
The same operation and measurement as in Comparative Example 3 were performed except that the base oil type, additive type, additive addition amount, and additive concentration were changed as shown in Table 1, and the results are shown in Table 1. Described.
（比較例７〜１０）
基油の種類、原料フラーレンの仕込み量、希釈基油の添加量、添加剤の種類、添加剤の添加量及び添加剤の濃度を表１に示したように変えた以外は実施例１と同様の操作及び測定を行い、表１に記載した結果を得た。
(Comparative Examples 7 to 10)
Example 1 except that the type of base oil, the amount of raw material fullerene charged, the amount of diluted base oil added, the type of additive, the amount of additive added, and the concentration of the additive were changed as shown in Table 1. The results described in Table 1 were obtained.
上記実施例・比較例の結果を表１に示す。 The results of the above examples and comparative examples are shown in Table 1.
表１に示すように、比較例と比べ、実施例では、摩擦係数が小さく良好な潤滑性を示すことがわかる。また、フラーレンを含有しない比較例３〜６、及び芳香族環を有しない添加剤とフラーレンを有する比較例３〜１０と比べ、実施例では特性が改善されているにもかかわらず粘度が上昇しないことがわかる。さらに、実施例のエステル油組成物では、長時間を放置しても長径１μｍ以上の粒子は１個未満であった。これは、凝集粒子を極力取り除くことおよび芳香族有する添加剤がフラーレンの凝集を抑制することにより、フラーレンのさらなる凝集粒の成長が抑えられたものと考えられる。
As shown in Table 1, it can be seen that, in comparison with the comparative example, in the example, the friction coefficient is small and good lubricity is exhibited. In addition, compared with Comparative Examples 3 to 6 not containing fullerene and Comparative Examples 3 to 10 having an additive and fullerene having no aromatic ring, the viscosity does not increase in the examples even though the characteristics are improved. I understand that. Further, in the ester oil compositions of the examples, the number of particles having a major axis of 1 μm or more was less than 1 even when left for a long time. This is considered that the growth of further aggregated particles of fullerene was suppressed by removing aggregated particles as much as possible and the aromatic additive suppressing the aggregation of fullerene.
Claims (7)
Furthermore, the manufacturing method of the ester composition of Claim 6 which has a 3rd process which dilutes the fullerene solution obtained at the 2nd process with base oil, and adjusts the fullerene density | concentration in an ester oil composition.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2020070961A1 (en) | 2018-10-03 | 2020-04-09 | 旭化成株式会社 | Conjugated diene polymer, branching agent, method for manufacturing conjugated diene polymer, extended conjugated diene polymer, rubber composition, and tire |
| CN111263802A (en) * | 2017-10-25 | 2020-06-09 | 昭和电工株式会社 | Lubricating oil composition containing fullerene and method for producing same |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111263802A (en) * | 2017-10-25 | 2020-06-09 | 昭和电工株式会社 | Lubricating oil composition containing fullerene and method for producing same |
| EP3702433A4 (en) * | 2017-10-25 | 2021-07-21 | Showa Denko K.K. | FULLEREN LUBRICATING OIL COMPOSITION AND METHOD FOR MANUFACTURING IT |
| US11905484B2 (en) | 2017-10-25 | 2024-02-20 | Resonac Corporation | Fullerene-containing lubricating oil composition and method for producing same |
| WO2020070961A1 (en) | 2018-10-03 | 2020-04-09 | 旭化成株式会社 | Conjugated diene polymer, branching agent, method for manufacturing conjugated diene polymer, extended conjugated diene polymer, rubber composition, and tire |
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